The largely unadorned, two-story Hugh Craft House (1851; 184 S. Memphis), also known as the Fort-Daniel Place, with its wrought-iron fence produced by the Jones-McIlwain company, has a board-and-batten outbuilding (c. 1855), which served as a slave dwelling and kitchen. Hugh Craft came to Holly Springs in 1839 as a surveyor for the American Land Company. Nearby at 127 W. Gholson, Crump Place (1836; later alterations) evolved from a log structure to become a wide, slightly raised Greek Revival cottage. At 248 S. Memphis, Burton Place (c. 1850), also known as Fleur-De-Lis, is a two-story Greek Revival brick house surrounded by a cast-iron fence (originally installed in the courthouse square) manufactured by the Jones-McIlwain Company. Behind the house and visible from Elder Avenue stands a three-room brick kitchen and slave dwelling (c. 1850).
The Norfleet-Cochran House (c. 1845; 154 W. Gholson), known as Dunvegan, was remodeled c. 1903 by Theodore C. Link, who added its Colonial Revival portico. Around 1917, its owners brought Link back to remodel two Greek Revival buildings west of Dunvegan as guest houses: the Featherston-Buchanan House (1837) and Polk-Cochran Place, known as Tuckahoe (1849) at 166 and 130 S. Craft Street, respectively. For both, Link employed an elegant neoclassicism and retained slave-related outbuildings.
At 151 S. West Boundary Street, the now-vacant Chalmers Institute (1837) is the oldest institutional building in the county and the second-oldest school building in the state. It first housed what was called a boys literary institute. With a certain local grandiosity, school officials renamed it the University of Holly Springs in 1838, but the institution closed in 1839. The school reopened a decade later as the Chalmers Institute and eventually became the Holly Springs Normal Institute. The brick building is large but plain, two stories tall, with a hipped roof, and ample windows. Today, it is owned by a local preservation organization.